Suzuki reaction on pyridinium N-haloheteroarylaminides: regioselective synthesis of 3,5-disubstituted 2-aminopyrazines
摘要:
An extensive study of Suzuki-Miyaura cross-coupling processes on N-pyridinium bromoazinyl aminides has been performed. Mono- and disubstitution on 5- and 3,5-bromo derivatives produced the corresponding aryl derivatives. In the disubstituted compounds regioselective substitution at the 3-position occurred, vicinal to the aminide nitrogen, and this was more evident in pyrazine derivatives. The commonly used strategy involving N-alkylation and reduction of the N-N bond gave rise to a series of 2-alkylamino-3,5-disubstituted-pyrazines. (c) 2007 Elsevier Ltd. All rights reserved.
New approaches to the synthesis of pyridinium N-heteroarylaminides
摘要:
Different substituted pyridinium N-heteroarylaminides have been prepared in one step from N-aminopyridinium iodide and the Corresponding heteroaryl halide by two alternative routes. The use of Pd catalysis allowed the easy preparation of products from the less reactive haloheterocycles. The use of water as a solvent in conjunction with microwave heating dramatically diminishes the reaction time without having an adverse effect on reaction yields. (C) 2008 Elsevier Ltd. All rights reserved.